


Nail Painting Party

by AsexualArchivist



Series: Critical Role Relationship Week [5]
Category: Critical Role (Web Series)
Genre: Gen, I love these fools, Nail Painting, These two need more bonding time!!!!, They talk about widomauk and fjorjester but they’re not in it so I won’t put it in the tag, sleepover time!!!
Language: English
Status: In-Progress
Published: 2018-06-23
Updated: 2018-07-03
Packaged: 2019-05-27 05:21:06
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 3,255
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15017513
Author URL: https://archiveofourown.org/users/AsexualArchivist/pseuds/AsexualArchivist
Summary: Jester teaches the rest of the Mighty Nein about self care using the best tool she has at her disposal: nail polish!(Originally for critical role relationship week but I just had so many Ideas I couldn't resist writing more!)





	1. Jester and Yasha

**Author's Note:**

> Whoops I missed yesterday but I’m gonna try to churn out another one by tomorrow!  
> This was so fun to write, I feel like I’m getting better at writing Jester!

It had been a long day. Yasha sighed and rubbed her eyes. Shopping trips were her least favorite part of traveling with the Mighty Nein. Just give her a gnoll or a merrow to cut in half; it would be preferable to listening to everyone haggle over potions or random magical items. Yasha just needed her sword and anything else was just over-complicating the whole process. 

She, Beau, and Jester were all sharing a room. Yasha like the girls; they were sweet, and didn’t mind when she had to leave again. She just hoped the other two would come back soon. Yasha wouldn’t be able to sleep until they got back; she was a light sleeper.

“Yasha! Today was fun, right?” Jester plopped down next to her. Yasha hadn’t even heard her come in.

“...yeah,” she said. She was fairly certain her impatience had been extremely obvious.

Jester giggled. “It’s okay, I’m an _expert_ shopper and even I get tired sometimes. My mom didn’t really let me go out, which I totally get because she was worried about me and was protecting me and I know it was for the best, but sometimes the Traveler would help disguise me so I could sneak out and buy things. I bought so many cute clothes, and jewelry, and art supplies...”

Yasha nodded. “There weren’t many... interesting places to shop where I grew up.”

“Well, now you can learn how fun it is!” Jester grinned. “Maybe you and I can go shopping together, just the two of us!”

“Uh...”

Jester laughed again. “No, I know you don’t want to, Yasha. It’s okay! I’ll still buy you something pretty if I see it.”

Yasha tried to hide her blush. “Oh... thank you.”

“Oh!” Jester sprung to her feet suddenly, causing Yasha to jump a little. “Speaking of pretty things...” and she pulled out a small red bottle with a flourish. Yasha stared blankly.

“I don’t... what is that?” She asked.

“It’s nail polish!” Jester gasped when she saw Yasha’s still-blank face. “Yasha! Have you never seen nail polish before??”

She shook her head. “Ah, no actually. What is it exactly?”

Jester sat down again. “Well, it’s special paint that you put on your nails to make them look all pretty! The Traveler and I used to paint each other’s nails all the time! Though mine never looked as pretty as his, because claws are kinda hard to paint. You can’t do any pretty designs on them, practically!”

“So...” Yasha started. “You just... put paint on your nails? So they’re pretty?”

Jester nodded excitedly. “Yeah! It’s really really fun. Oh!” She squealed, an idea apparently coming to her. “Yasha, pretty pretty please will you let me paint your nails? I’ll even paint some pretty flowers on them, if you want.”

Yasha smiled at her beaming face. “Sure, I suppose that would be... pretty fun.”

Jester let out another squeal and pulled a couple of small bottles from her bag. “This is just like a sleepover! Ooooh, maybe when Beau gets back I can paint her nails too! I think she would look so pretty with blue nails to match her outfit! Of course, Beau is already very pretty but it would be so cute if she matched-“

Yasha smiled. “Yes, I think she would like that. Do you have black?”

“Let’s see, I have reeeeeeeddd, bluuuuueeee, greeeeeeen, goooooooolddd... no, I don’t think so! But how about this dark purple?” She held up a vial of dark liquid.

Yasha stared at Jester. “Why did you get so many colors? And why would you get blue if your skin is blue? It would just blend in.” The dark blue flush forming on Jester’s cheeks made Yasha grin. “Were you planning this whole slumber party?”

“Well-“ she started, flustered, “I mean, _maybe_ I thought it would be cool to get everyone together in a group and do sleepover things... like ghost stories... and maybe talk about crushes and first kisses and stuff... you know!”

Yasha just tilted her head. “I don’t. I’ve never had a sleepover before.”

“Me either!” Jester sighed. “Well, unless sleepovers with the Traveler count. I don’t think they should, though, we didn’t talk much about crushes at all.”

Yasha shifted on the bed, thinking. “Do you... want to get the others in here? To have a sleepover with?”

Jester thought for a moment, then shook her head. “No, I think maybe this sleepover’s just for us. It can be both of our first sleepovers!” She gave Yasha a little wink, then giggled. “Ok, I’m going to paint your nails the prettiest they’ve ever been!”

Jester chatted about the rest of the Mighty Nein, telling Yasha what colors of nail polish would look best on them. “-and I got this red for Caleb, because he does all that fire stuff! Maybe he would even let me put little flames on his nails, it would be so cute! And Molly would be gold because he’s so flashy all the time. And then- hmm, what color do you think Fjord’s nails would be?”

“Maybe... yellow?” Yasha said, a question in her voice. 

Jester smiled wide. “Yes! Yellow would looks so pretty with his green skin! And I would maybe put little hearts on them... oooooh! Do you think Caleb would let us paint Frumpkin’s claws?”

Yasha had to smile at the mental image of Frumpkin and Caleb with matching nails. “We could always ask. I think he would. He seems to like you, Jester.”

Jester screwed up her face. “Ewwwww, Caleb’s sweet but he’s too stinky for me.”

Yasha laughed. “No, I mean, he thinks of you as a friend. We all do, Jester.”

“Oh! I- um, really?” Jester looked a little nervous, like she was afraid Yasha might take it back. Yasha nodded, though, and looked into her eyes.

“Yes. You are a good friend, Jester. And I’m not just saying that because I haven’t had very many friends.”

“Oh...” Jester sniffed once, almost unnoticeable. “I haven’t really... had friends before, besides the Traveler. I wasn’t sure if I was doing this right.”

Yasha laughed softly. “Neither am I. And I’m sure at least Caleb and Beau and Nott feel the same. But I think you’re doing a good job. For... for what it’s worth.” She looked down, suddenly embarrassed. “Sorry. I’m- not good with people.”

She looked up to see Jester quickly scrubbing at her eyes with her sleeve. “Did I make you cry? I’m sorry-“

“No, no, these are happy tears.” Jester sniffled again. Yasha tried to lift up her hand to give her an awkward pat on the back, but Jester screeched at her. “Stop! Stop, don’t mess up the nail polish!”

“Oh- okay.” She let her hands hover around Jester in an air hug. She patted the air a couple of times for good measure, then carefully lowered her arms again.

“Well, I’m almost done,” Jested continued as if nothing had happened. “I just have to add a clear coat! It helps the polish stay on longer!”

Yasha nodded, pretending she understood the purpose of clear nail polish. Jester quickly finished applying the last of it and leaned back, smiling. 

“I think it turned out pretty good!”

Yasha looked at her nails and stared. They were a beautiful dark purple, with small white and gold flowers adorning them in small clusters. She was almost afraid to move her hands, lest she smear them. She had never had something so beautiful on her body before. She didn’t know it was _possible_ for anything about her to be this... pretty. 

“Jester... thank you. This is beautiful.”

Jester beamed. “I’m glad you like it! Oooooh, maybe this can be our ‘thing’ from now on, we can sit around and paint our nails and talk! It would be so fun!!!”

Yasha found herself grinning as well. “I think I would like that. Maybe you can teach me how to do this?”

“Of course, Yasha! Then we can take turns painting each other’s nails like _friends_ do!”

Yasha, still smiling ear to ear, nodded. “Yes. Friends.”


	2. Jester and Caleb

**Summary for the Chapter:**

> Caleb and Jester..... talk about boys :3c

**Notes for the Chapter:**

> hey! I'm gonna be adding more to this because I just thought it was such a cute idea!  
> I don't know if I'll do everyone but i might!

"Caaaaaaaaaaleeeeeebbbbbb!"

Caleb pretended to be asleep. It was easy, considering he was about ten seconds away from actually falling asleep.

"Caleb! Wake up!"

"Ughhhhh......." Caleb groaned, pulling his pillow over his head. Suddenly the pillow was gone and he was staring into blue, pupiless eyes. Jester smiled.

"You're awake!" She plopped down on the bed next to him, ignoring his feeble attempts to wrest the pillow from her grasp.

"Jester..." Caleb pleaded. He considered just laying back down without the pillow. His eyes were just about to close when Jester spoke up again.

"I wanted to check on you," she said, folding her arms over the pillow now in her lap. "You almost _died_ today, Caleb."

He shrugged. "All of us almost die all of the time."

Jester pouted, flopping over so that she landed on top of Caleb's legs. "But you're so squishy! I'm worried one of these times you're just going to fall over and not get up!"

Caleb sat up, resisting the urge to shrug again. "Well, you have that spell you can use, _ja_? The one where you bring people back to life? So I will be fine, even if I am... squishy."

"I guess..." Jester sighed.

Caleb nodded. "You are a good healer, Jester. I trust you."

She smiled gratefully at him, and Caleb felt a warmth in his chest with the knowledge that he had correctly conveyed what he was feeling. Usually he fucked up things like this. But Jester was smiling, and now he was smiling, and Caleb got the distinct impression that he had done something right.

After a moment, Jester sprung up. "You know what cheers me up after I almost die?"

"It happens often enough for you to need a specific pick-me-up?"

"Nail painting!" she exclaimed, ignoring Caleb completely. She rummaged in her bag for a moment, then pulled out a vial filled with thick orange liquid. "Pleeeeeeaaaaaaase let me paint your nails for you, Caleb!"

He stared for a moment. "I... have never done this before." He thought he remembered his mother painting her nails once or twice, but she only did that for special occasions.

Jester's smile brightened. "Well, I can be your first time!" She winked at him suggestively. Caleb blushed deep red, causing Jester to giggle. "Don't worry, I'm _very_ good at it. I used to paint my mother's nails sometimes when she had really really rich clients come over. She said she liked the way I did it more than anyone else." Jester's eyes shone with pride, and Caleb had to fight back the two competing emotions of jealousy and wistfulness. She really loved her mother.

Despite his uncertainty, he held out his hands towards Jester in a tacit agreement. She squealed with delight, swirling around the orange vial before uncapping it to reveal that it had a brush attached to the inside of the lid. She took one of Caleb's hands, squinting with distaste.

"Ewwwwww Caleb, your hands are so dirty!"

He shrugged. "I like being dirty."

"Can you at least wash them off a _little_ before I do this? I don't want my nail polish getting all dirty and stinky." She stuck out her tongue at him.

Caleb thought for a moment. "... _Nein._ " He grinned at her exasperated expression. 

Jester shook her head and sighed. She started on his right hand, carefully covering every inch of his dirt-encrusted nails in bright orange polish. Caleb watched her, entranced. She was so focused on her task, so methodical, like him when he transcribed his spells. He had never seen Jester look so intently at anything before.

Before long, though, the spell was broken as Jester spoke.

"So, Caleb, you're always so dirty and smelly so I can see why you've never painted your nails before. You don't really take care of yourself! You need to start washing your face at least or you will get _so_ much acne. I used to have acne all over my face when I was younger, I didn't really leave the house very much so nobody really saw it but it was _so_ gross! My mom said that it was all a part of growing up though so I didn't really mind, and the Traveler told me that I still looked pretty when I asked him, so it probably wasn't even that big of a deal."

"My mother used to tell me that, too," said Caleb fondly. "About it being a part of growing up."

Jester nodded enthusiastically and kept talking. "I know, my mom is full of so much wisdom like that. She's really smart. She talked to me all the time about her work and how to be safe and how to tell men to fuck off if they wanted to mess with me. When I was older she would always teach me stuff about safe sex, and how to make sure you and your partner were both having fun, the best positions for when-"

Jester stopped, apparently noticing Caleb's face. It was beet red, almost as red as his hair. "It's just sex, Caleb! It's not gross! My mom always said that sex is a beautiful, natural part of life!"

"I know, but can we talk about something else, please?" Caleb asked, feeling his face growing hotter.

"Okaaaaaaaaaay, but if you need any pointers any time you can always ask me! My mom taught me _a lot_ of important things." Jester worked in silence for a moment, before it seemingly became too much for her. "My mom also talked a lot about romance... She didn't get much of a chance for romance because she was so popular and people would try to romance her to get her to themselves. But she _really_ loved my dad. She talked about him like he was the most beautiful and sweet tiefling in the world! You know, she told me that before they were dating, he would send her different flowers every day, with a note about a different thing he thought was beautiful about her." Jester sighed, reaching for another bottle of polish, this one yellow. "I want someone to send me flowers every day..."

"Do... people like that?" Caleb asked. Maybe, if people liked flowers that much, he should... no, that would be stupid. He blushed at the thought. Jester gave him a look.

"What are you thinking about over there? You're blushing again. This isn't even sexy stuff!"

"Nothing!" He said too quickly, then winced. Jester broke into a grin.

"Caleb... is there somebody you want to give flowers to?"

He shook his head violently. "No!"

Jester's grin could now fall under the category of "shit-eating". "You have a crush!"

Caleb looked around the room for an escape route, but found none. "I do not, that is... that is silly, Jester. Who would I have a crush on?"

Jester thought for a moment. "Well, it can't be Beau, because she's obviously in love with Yasha. And obviously not Nott either. And Yasha is pretty cool but I don't think you're into her that way, which is good because she and Beau would be sooooooo cute together! That leaves me and Fjord and Molly, but, no offense Caleb, but I don't think of you in that way."

"None taken," he said, dazed. "I do not... swing... that way. As they say."

Jester nodded knowingly. "So that leaves either Fjord or Molly, and judging by the way you call him 'Mister Mollymauk'..." she grinned even wider. "I think I know who it is!"

Caleb was blushing so hard now that he was worried his skin would melt from the heat. " _Ja,_ okay, I... I might have a crush on Mollymauk."

Jester squealed, putting aside the nail polish. "Caleb! That's so cute! Are you going to do something for him? Maybe get him something?"

He shook his head, sighing. "I... am not good at this, Jester. Not like you. I have been out of the game for some time."

"I can help you!" she replied, scooting closer to him. "I'm really really good at relationship stuff. You just need to spend some time alone with him and tell him how you feel!"

" _Nein_ ," Caleb said quickly, "I will not tell him. Not yet. I am not ready for that." _He deserves better than me,_ he thought. _Better for me to suffer alone then for him to accidentally love a monster._

Caleb's face must have betrayed some of his thoughts, because Jester frowned. "You don't have to, Caleb. You can talk to me, though, if you need advice." She picked up another bottle of polish, this one clear, and set to work again.

Surprisingly, it was Caleb who broke the silence this time. "What about you, Jester?"

"What about me?" she replied, not looking up from her task.

"Aren't you crushing on someone in the Mighty Nein as well? Someone... green?"

Jester stuck out her tongue. "Nott is just a friend, Caleb, no need to get jealous!"

He shook his head, ignoring her laughter. "You know who I mean, Jester. You and Fjord seem... very close."

She just laughed again. "We're friends! I flirt with my friends sometimes. I flirt with you!" Jester seemed to be trying to convince herself as much as him.

"It is alright if you do, Jester. Fjord is a good man. I think he might like you, too."

Now it was Jester's turn to blush. "Ugh, Caleb! When did you get so good at this!"

"At what?" He gave her a quizzical look.

"At, like, being supportive and stuff!" She sighed. "I don't know if I'm even really into him, or if he's even really into me."

Caleb was no expert at relationships, but he tried his best anyway. "You got very jealous in the swamp when that lady called Fjord attractive. And again in Huperduke. So, I think you might have feelings for him, Jester."

Jester flopped over again, apparently finished with Caleb's nails. "Ughhhhhhhhhh you're right. You're right! I'm into him." Jester sighed again. "Fuck, it's more fun when _I'm_ the one doing the pestering!"

Caleb laughed softly at that. "I will not tell anyone, if you promise not to tell anyone about... you know." He coughed awkwardly.

Jester grinned. "Sounds like a plan! Oh, I'm done with your nails, by the way. Do you like them?"

Caleb looked down for the first time at his nails. They were gorgeous; the orange and yellow flames dancing across them almost looked real. He hadn't ever done anything this nice for himself before.

"They are beautiful," he said, smiling with gratitude. "Thank you, Jester."

She smiled too. Then she yawned, stretching her arms above her head.

"I'm super sleepy now, so I'm gonna go... you have to wait for a little while for the nail polish to dry before you go to sleep! Don't mess up my beautiful art!"

Caleb sighed. He was so tired, but he didn't want to risk messing up his beautiful new nails. "Okay."

"Goodnight, Caleb!" She waved, smiling, as she left the room.

"Goodnight, Jester." Caleb smiled back, admiring again the time and effort she had put into making his nails look so pretty. No one had ever done anything like that for him before, not since his parents.

After Caleb felt like enough time had passed, he laid down again and closed his eyes, falling asleep almost immediately. He slept soundly for the first time in weeks.

**Author's Note:**

> Thanks for reading! Comments and kudos always appreciated <3


End file.
